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Clearwater - an experiment project

This is a small town I have been rolling around recently. I will not not update it any further as it was just for experimenting (and I had messed up with my layers at some point and the houses are not fully editable anymore). All the houses have reddish tile roofs because that way it was easier to experiment but I plan on having more roof types in the next map.
I will start a new project some time soon based on this same technique but before I begin, I sure need to find out some automated tricks to speed things up as this way a larger city would take forever.

Thanks guys.
For this experiment I created few different roof types and I also made a set of roof items (chimneys, attic windows etc). The actual roofs are made by combining these items and the hard part is the amount of manual drawing needed to avoid repeating things too much.

I created the items in higher resolution and then I made them smaller to hide any issues with matching them together. This way I can fool the eye to see them rather natural.